Detergent composition



Patented Aug. 28, 1945 DETERGENT COMPOSITION Nathaniel Beverley Tucker,Louisville, Km, assignor to The Procter & Gamble Company, Cincinnati,Ohio, a corporation of Ohio No Drawing. Application July 2, 1942,

a Serial No. 449,496

22 Claims.

The present invention relates to cleansing, washing and launderingcompositions of improved efficiency and to the process of producing thesemen.

It is an object of my invention to improve the cleansing power ofdetergent compositions comprising as the essential detergent materialwatersoluble organic sulfuric acid derivatives containing a sulfate orsulfonate group.

Another object is to prepare detergent compositions of superiorcleansing and detergent properties.

Other objects will be apparent from the following description of myinvention.

I have found that certain new compounds closely related to each otherare outstandingly effective for increasing the cleansing action ofsulfate and sulfonate detergents, especially in the washing of woolenfabrics. These compounds are amides having the formula wherein RrCO isthe acyl radical of a fatty acid having ten to fourteen carbon atoms, Ris selected from the group consisting of hydrogen, methyl, ethyl, andmethylol, and each R is selected from the group consisting of hydrogenand methyl. By themselves these amides, which may be referred to asamides of -amino 1,3-dioxanes, are not laundering agents, but when addedto a detergent of the class above above named they markedly enhance thecleansing efl'ect thereof. For this purpose the amides described aboveare in a different class from those preparations such as stearamide andpalmitamide which have heretofore been proposed for use withwater-soluble compounds in the softening of textile.

Examples of amides which come within the scope of the above generalformula and which may be employed in the practice of the presentinvention are the lauramide of 5-amino 5-methyl 1.3-dioxane, thecapramide of 5-amino 5-ethyl 1,3-dioxane, the lauramide of 5-amino5-ethyl 1,3- dioxane, the myristamide of 5-amino 5-met-hylol1,3-dioxane, the lauramide of 5-amino 2.5-dimethyl 1,3-dioxane, thelauramide of 5-amino 5- methylol 2,2-dimethyl 1,3-dioxane, the capramideof 5-amino 4,5-dimethyl 1,3-dioxane, the capra mide of 5-amino5-methylo1 2,6-dimethyi 1,3-dioxane, and corresponding amide mixturesprepared from fatty acid mixtures consisting predominantly of fattyacids having ten to fourteen carbon atoms, such as .those mixturesobtainable from oils of the coconut oil type. of which coconut oil andpalm kernel oil are well known examples. The above amides may beprepared from the corresponding amines, which may be synthesized inaccordance with U. S. Patent 2,247,256, issued June 24, 1941, to Senkus,and fatty acid chlorides having ten to fourteen carbon atoms in the acylradical, as follows:

A mixture of 100 parts water, 6 parts sodium carbonate and 12.9 parts5-amino 5-ethyl 1,3- dioxane is prepared and cooled to 0 C. To thismixture are added dropwise 21.8 parts iauroyl chloride, the temperatureof the reaction mixture being maintained at about 0 C. After all lauroylchloride has been added the mixture is dissolved in ether and washedwith 4% sodium carbonate solution and then with water. The washedmaterial is then dried and the amide recovered by evaporation of theether solvent.

The invention is applicable to the improvement of all detergents comingwithin the class above mentioned, the advantage of the invention beingthe improvement in the cleansing power of those sulfates and sulfonatesalready characterized by substantial power to cleanse rather than theconferring of cleansing power on those materials such as wetting andsoftening agents which are inactive as detergents.

outstandingly interesting detergent compounds with which the aboveamides may be used with advantage are the water-soluble salts of thehigher molecular weight alkyl sulfuric acids which have distinct andpronounced detergent power making the product suitable for use incleansing and laundering operations. Thus the invention isparticularlyapplicable to the improvement of the already knowndetergents in which the principal active constituent is a water-solublesalt of other alkyl sulfuric acids having decided detergent value andhaving eight to eighteen carbon atoms in the alkyl radical are improvedby the addition of the amides of the 5-amino 1,3-dioxanes hereincovered, and especially are these amides useful in -acid amide ofN-methyl taurine).

improving the detergent power 'of the salts of those alkyl sulfuricacids derived from a mixture of higher alcohols obtained from oils ofthe coconut oil type such asecgconut oil, palm kernel oil,

etc.

Besides the alkyl sulfate detergents referred to above other compoundshaving a sulfuric acid ester group and value as washing and detergentagents in aqueous solution are improved sulfonate group, these compoundspossessing a substantial power to wash and cleanse in aqueous solutionin the absence of an enhancing agent. For example, beneficial resultswill be noted when the amides are employed with water-soluble salts ofhigher fatty acid esters of 1,2-dihydroxy propane il-sulfonic acid, thesodium salt of the coconut oil fatty acid ester being an excellentexample of this type of detergent. Beneiicial results will be noted alsowhen the amides of the S-amino 1,3-dioxanes and their derivativesa,ses,vse

Example 1.To 95 parts of a commercial detergent containing as. activeingredient 40% of the sodium salt of the sulfuric acid ester preparedfrom the higher alcohols obtained by the reduction of coconut oil, areadded parts of the lauramide of 5-amino 5-ethyl 1,3-dioxane. The

- detergent thus preparedis much superior to the commercial detergentalone in cleansing operations.

Example 2.A superior detergent coming within the scope of the presentinvention is prepared by mixing 90 parts of the commercial alkyl sulfatedetergent employed in Example 1 with 10 38% sodium salt of oleic acidamide of N-methyl as above defined are employed with such deter- 1 gentsas the water-soluble salts of the higher fatty acid monoesters of lowermolecular weight hydroxyalkyl sulfonic acid (oleic acid ester of thesodium salt of isethionic acid) and of the higher fatty acid amides oflower molecular amino alkyl sulfonic acids (ammonium salt of oleicLikewise the amide may be employed with water-soluble salts of thehigher alcohol esters of suli'ocarboxylic acids (sodium salt of thelauryl alcohol ester of suifoacetic acid), higher alkylated benzenesulfonic acids (potassium salt of the sulfonic acid derived from thecondensation product of benacne and a chlorinated kerosene fractioncontaining predominantly twelve carbon atoms per molecule), and ethersof high molecular alcohols and lower hydroxy sulfonic acid (monolaurylether of 1,2-dihydroxy propane 3-sodium sulfonate).

' do not Wish to be limited thereto.

In the practice of my invention, the amide usage will vary depending onthe specific combination of ingredients, but in general the quantity ofamide will be less than the quantity of active detergent ingredient. Iprefer to employ from about eight to about twenty per cent of amidebased on the active detergent, but marked improvement can be obtainedwith smaller proportions and larger proportions, for example proportionswithin the range from about five per cent to about fifty per cent.

The invention will be more clearly understood from the followingexamples, but these examples are merely illustrative of the manner inwhich my invention may be practiced and are not tobeconstruedaslimiting. Allpartsareby weight.

taurine as active ingredient with 10 parts of the lauramide of 5-amino5-ethyl 1,3-dioxane.

Example 5.-To parts of a commercial detergent containing 38% of thesodium salt of the ester of sulfoacetic acid and the mixture of higheralcohols obtained from coconut oil by reduction are added 10 parts ofthe lauramide of 5- amino 5-ethyl 1,3-dioxane. The resulting mixture hasdetergent power superior to the suiteacetic acid ester without amide.

Example 6.An improved detergent is prepared by mixing 90 parts of adetergent containing as active constituent 38% of the coconut oil fattyacid monoester of 1,2-dihydroxy propane 3-sodium sulfonate with 10 partsof the lauramide of 5-amino 5-ethyi 1,3-dioxane.

Example -7.A detergent of superior washing power, especially on wool, isprepared by mixing 90 parts of a commercial detergent containing asactive constituent the coconut oil fatty acid monoester of 1,2-dihydroxypropane 3-sodium sulfate with 10 parts of the lauramide of 5-amino 5-"ethyl 1,3-dioxane.

Highly eflicient washing agents will result if instead of the specificamides used in the above examples, any of those amides referred to inthe general description of the invention is employed.

I have repeatedly referred to the superior washing power of detergentsprepared in accordance with my invention and wish to emphasize here thatthis superiority is apparent to the user and represents a source ofsubstantial saving in detergent usage. For example, detergents such asthose of the above specific examples, that is, commercial detergent inadmixture with the amides of 5-amino 1,3-dioxanes, when employed in 0.2per cent concentration in hard water, a. normal concentration used inlaundering, will wash much whiter than any concentration of thecommercial detergent without added amide. In general, a solutioncontaining any given concentration of a cleansing compound prepared inaccordance with the present invention will wash as white as, or whiterthan, a solution containing a much larger concentration of detergentwithout added amide.

My invention is not limited to any particular method of mixing the amidecompounds with the essence 3 pounds to water prior to the adding of thedetergent, or vice versa, or to add both amide and detergentsimultaneously but water. I

Having thus described my invention, :what I claim and desire to secureby Letters Patent'is:

l. A cleansing and laundering comprising essenuauy a mixture ofswam-solufole' salt of an organic sulfuric having in itsmolecularstructurea" radical aelected from the group consisting ofsuli'onic acid and sulfuric acid ester radicals. the said salt havingpronounced .deterge'nt power. and. an

amide having the following general formula m-co-Nn came-o a wherein RrCOis the acyl of a fatty separately to claimed in claim 1, in which theacyl radical of the amide i derived from lauric acid.

.8. A cleansing and laundering composition claimed in claim 1, in whichthe acyl radical of the 5 amide is derived from myristic acid.

;'l. A cleansing and laundering composition claimed in claim 1, in whichthe amide is the lauramlde of li-amino 5-ethy1 Lit-diorama.-

.8. A cleansing and laundering composition claimed in claim 1, in whichthe amide is the myristamide of B-amino ii-ethyl 1.3-dioxane. v 9. Acleansing and laundering composition inclaim 1, in which the amide isthe on fatty acid amide of Ii-amino fi-methyl l5 LS dioxane.

1 A cleansing and laundering composition in claim 1, in which thedetergent. material. is 'ja water-soluble salt of an aliphaticsulfin'icja'cidester containing eight to eighteen carurainide of ii-amino li-ethyl 1,3-dioirane.

, cleansing and laundering composition in; claim 1, in which thedetergent materialjis the water soluble salt of an alkyl sulfuric g5-acid derived-from higher alcohols obtained from coconut on and the amideis the lauramide of 5- amino li-ethyl l,3'-dioxane.

- i2, Ajcleansin'g and laundering composition claimed in claim 1, inwhich the detergent mathe' alkyl radical, and the amide isfhaving 10 to14 arbon atoms, R i selected 3o "terial ita'w'ater-soluble salt of analkyl sulfuric the group consisting of hydrogen, methyl, mech- ,facid{derived from the higher alcohols obtained y lol, and ethyl. and each Ris selected from the from coconut oil and the amide is the lauramide ofgroup consisting of hydrogenandinethyl. the amount by weight of theamide being less .thanthe amount by weight of. the said detergent niaterial but sui'ilcient to enhance thedetergcnt power thereof.

2. A cleansing and laundering composition comprising essentially amixture of a detergent selected from the group consisting ofwater-soluble salts of: higher alkyl sulfuric acids, higher fatty acidesters of lower molecular weight hydroxy alkyl sulfonic acids, higher.fatty acid amides of low molecular amino alkyl sulfonic acids, higherfatty acid monoglyceride sulfuric acids, higher alcohol esters ofsulfocarboxylic acids, higher alkylated benzene sulfonic acids, higheralcohol ether; of low, molecular hydroxy alkyl sulfonic acids, andhigher fatty acid alkylolamide sulfuric acidaand an amide of the formulaR1.C0-NH CH(R')- 0 a l n on n' -o n' wherein Rl'CO is the acyl radicalof a fatty acid having 10 to 14 carbon atoms, R. is selected from thegroup consisting of hydrogen, methyl, methylol, and ethyl, and each R isselected from the group consisting of hydrogen and methyl, the amount byweight of the amide being less than the amount by weight of the saiddetergent material but sufficient to enhance the detergent powerthereof.

3. A cleansing and laundering. composition claimed in claim 1, in whichthe acyl radical of the amide is derived from a mixture of fatty acidsconsisting predominantly of lauric and myristic m-co-Nn sj-ommo.B-methyl 1,3-dioxane.

d3. A cleansing and laundering composition 135.: comprising essentiallya mixture of. a water-solu- ,ble salt of the coconut oil fatty acidmonoester of 4' 1,2-dihydroxy propane 3-sulfonic acid, and an amide ofthe formula m-co-Nn omao-o B 5 from' the group consisting of hydrogen,methyl, methylol. and ethyl, and each R is selected from the groupconsisting of hydrogen and methyl, theweight of the amide being lessthan the weight of the said water soluble salt but sufllcient to enhanocthe detergent power thereof.

14. A cleansing and laundering composition comprising essentially amixture of a water-soluble salt of coconut oil monoglyceride sulfuricacid ester and an amide of the formula cums-0 a v n cnum-o R whereinRr-CO is the acyl radical of a fatty acid 0 having ten to fourteencarbon atoms, R is selected from the group consisting of hydrogemmethyl,methylol, and ethyl, and each R. is selected from the group consistingof hydrogen and methyl, the weight of the amide being less than theweight of the said. water soluble salt but suillcient to enhance thedetergent powerthereof.

15. As a detergent improving agent possessing the power to enhance thecleansing efficiency of organic sulfate and sulfonate laundering agents,

especially on woolens, an amide of the formula to wherein ai-co is theacyl radical of a fatty so.

especially on woolens, an amide of the formula R/ cmn'i-o wherein R1-COrepresents the acyl radicals of a mixture of fatty acids derived fromcoconut oil and consisting predominantly of lauric and myristic acids, Ris selected from the group consisting of hydrogen, methyl, methylol, andethyl, and each R is selected from the group consisting of hydrogen andmethyl.

17. As a detergent improving agent possessing the power to enhance thecleansing efllciency of organic sulfate and sulfonate laundering agents,especially on woolens, the lauramide of S-amino 5-methyl 1,3-dioxane. ,7

18. As a detergent improving agent possessing the power to enhance thecleansing efllciency of organic sulfate and sulfonate laundering agents,especially on woolens, the myristamide of 5-amino 5-ethyl 1,3-dioxane.

19. As a detergent improving agent possessing the power to enhance thecleansing eiliciency of organic sulfate and sulfonate laundering agents,especially on woolens, an amide derived from a mixture of higher fattyacids contained in coconut oil and consisting predominantly of lauricand myristic acid, and 5--amino S-methyl 1,3- dioxane.

20 A cleansing and laundering composition comprising essentially amixture of a water soluble salt of an alkyl sulfuric acid having eightto eighteen carbon atoms in the alkyl radical and having pronounceddetergent power, and an amide of the formula c R CH(B')-0 \R wherein R100 is the acyl radical of a fatty acid having ten to fourteen carbonatoms, R is selected from the group consisting of hydrogen, methyl,methylol, and ethyl, and each R is selected from the group consisting ofhydrogen and methyl, the amount by weight of the amide being less thanthe amount by weight of the said water soluble salt but suflicient toenhance the detergent power thereof.

21. A cleansing and laundering composition claimed in claim 1 in whichthe amount of the amide is from about 5 per cent to about per cent byweight of the detergent material having pronounced detergent power.

22. A cleansing and laundering composition claimed in claim 1 in whichthe amount of the amide is from about 8 per cent to about 20 per cent byweight of the detergent material having pronounced detergent power.

NATHANIEL BEVERLEY TUCKER.

